Methanol → HCID 178521923, Verbindung

To a solution of 2-methoxy-N-phenylisonicotinamide (1.00 g, 4.38 mmol) in anhydrous chloroform (60 mL) was added iodotrimethylsilane (17.50 g, 87.50 mmol). The reaction mixture was stirred at reflux for 16 hours. After cooling to ambient temperature, methanol (10 mL) was added dropwise to quench the reaction. The solvent was removed in vacuo. The residue was dissolved in ethyl acetate (300 mL) and washed with saturated aqueous sodium bicarbonate solution (2×100 mL) and brine (150 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrate in vacuo. The brown crude product was recrystallised from ethyl acetate and methanol to afford the title compound as a colourless solid (0.35 g, 19%): 1H NMR (300 MHz, DMSO-d6) δ 11.88 (br s, 1H), 10.31 (s, 1H), 7.73-7.68 (m, 2H), 7.47 (d, J=6.8 Hz, 1H), 7.31 (t, J=7.9 Hz, 2H), 7.10-7.05 (m, 1H), 6.81 (s, 1H), 6.49 (dd, J=6.8, 1.7 Hz, 1H); MS (ES+) m/z 215.2 (M+1).